2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-Ethyl-N'-[7-(phenylsulfanyl)-1,3-benzothiazol-2-yl]urea

HRID 9160Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH2:13][CH2:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

To a mixture of N-ethyl-N′-[7-(phenylsulfanyl)-4,5-dihydro-1,3-benzothiazol-2-yl]urea (crude product from the previous reaction, 1.59 mmol) in toluene (35.0 mL) was added DDQ (500 mg, 2.17 mmol). The reaction mixture was stirred at about 20° C. for about 2 hrs. The toluene was removed in vacuo and the crude material was taken up in CH2Cl2. The organic phase was washed with 0.5 M NaOH (2 times) and dried over MgSO4. The crude oil was purified by flash chromatography on SiO2 (EtOAc/CH2Cl2 5/95). 445 mg (85%, 2 steps) of pure product was isolated. LC/MS 330 (MH+); RP-HPLC RT 17.56 min.

Workup

customThe toluene was removed in vacuo
washThe organic phase was washed with 0.5 M NaOH (2 times)
dry with materialdried over MgSO4
customThe crude oil was purified by flash chromatography on SiO2 (EtOAc/CH2Cl2 5/95)
custom445 mg (85%, 2 steps) of pure product was isolated

Sources & evidence

ORD record: ord-955b7113daa34b80b77e74e52f6c7686
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Reaction notes

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